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The Underworld Podcast

The First Gangster Kingpin of New York

The Underworld Podcast

The Underworld Podcast

True Crime, Documentary, History, Society & Culture

4.71K Ratings

🗓️ 17 February 2026

⏱️ 62 minutes

🧾️ Download transcript

Summary

Monk Eastman ruled the depraved streets of turn-of-the-century Manhattan with fists and absolutely zero regard for human life, commanding an army of 1,200 thugs who terrorized the Lower East Side. At the height of his power, he was pulling cash from every racket you could think of while rigging elections for Tammany Hall and overseeing street violence so extreme that cops needed reinforcements just to enter his territory. Eastman represented a true transition in the evolution of the underworld, when crime became organized. All that, and he managed to become a war hero too, before the street life finally caught up with him. Learn more about your ad choices. Visit megaphone.fm/adchoices

Transcript

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0:00.0

I'm Richard Serrett. Join me on Strange Planet for in-depth conversations with the world's top paranormal investigators, alien abductees, bigfoot trackers, monster hunters, time travelers, and more.

0:11.1

The handler one day told her this whole thing about how they've been terraforming on Mars, and they're building a colony,

0:16.7

and they're recruiting specific people of specific bloodlines and specific talents and skill sets to go onto the planet.

0:23.0

On Richard Serrett's strange planet, we're redefining reality. Listen now wherever you get your podcasts.

0:34.6

November 1903 in an abandoned barn on the outskirts of the Bronx. A gang war is brewing on

0:41.9

the streets of downtown Manhattan between the two most powerful men in New York City. It's actually

0:47.8

almost like a real war, because both men have thousands of soldiers underneath them, and when

0:52.9

they clash on the streets, there are

0:54.5

pitch battles that can last all night.

0:57.8

What's happening here, though, is actually an attempt to stave off those battles.

1:01.9

Because election season, when the two men put aside their differences and used their street

1:06.5

soldiers to help get the corrupt politicians that protect them elected, has just ended.

1:11.1

And there's trouble brewing over some territory.

1:13.8

Very profitable territory.

1:16.1

You see, there's about to be a boxing match in this barn, one that all the politicians

1:20.7

and high-up police officials have basically begged the two men to have.

1:24.5

Because the two men in the center of this dirt ring in the middle of nowhere,

1:28.4

surrounded by hay bales, are Monk Eastman and Paul Kelly. And instead of sending their two gangs

1:33.6

to battle it out all over the streets in New York, they've agreed to settle it man to man, kingpin

1:38.8

to kingpin in the ring, the victor claiming the disputed territory they've been fighting over for years.

1:45.4

That territory has New York City's Bowery as its center point, the city's Red Light District.

1:51.1

This is the days of the East and West Village being depraved like none other.

...

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